Patent GB-957842-A (GB)
Title: New substituted phenols
Inventor: HURLOCK RONALD JAMES
IPC: C09K15/30
Filed: 1961-04-26
Abstract: The invention comprises phenols substituted in each of the 2, 4 and 6 positions by substituents of which one is a benzthiazylthioalkyl group of formula: <FORM:0957842/C2/1> where R and R1 are hydrogen atoms or alkyl groups and the nucleus A may be substituted by a chlorine atom or an alkyl, alkoxy or alkylamino group, the second is another such benzthiazylthioalkyl group or a tertiary alkyl or alkylcycloalkyl group, and the third is an alkyl group having up to 9 carbon atoms, an alkylene group joined to another phenol nucleus bearing a benzthiazylthioalkyl group, (which phenol nucleus is optionally substituted by a chlorine atom), or a cycloalkyl, alkylcycloalkyl, or aralkyl group, and their preparation by reaction of a mercaptobenzthiazole, an aldehyde or ketone and a phenol, in any order, and preferably in the presence of an acidic or basic catalyst. The compounds of the invention are used as anti-oxidants and antiozonants for natural and synthetic rubbers, rubber articles and latices, polymers and mineral oils.ALSO:Antioxidant and antiozonant stabilizers for natural and synthetic rubbers and other polymers comprise phenols substituted in each of the 2, 4 and 6 positions by substituents one of which is a benzthiazylthioalkyl group of formula: <FORM:0957842/C3/1> where R and R1 are hydrogen atoms or alkyl groups and the nucleus A may be substituted by a chlorine atom or an alkyl, alkoxy, or alkylamino-group, the second is another such benzthiazylthioalkyl group or a tertiary alkyl or alkylcycloalkyl group, and the third is an alkyl group having up to 9 carbon atoms, an alkylene group joined to another phenol nucleus having a benzthiazylthioalkyl substituent, (said phenol being optionally substituted by a chlorine atom), or a cycloalkyl, alkylcycloalkyl or aralkyl group (see Division C2).  The substituted phenol is preferably used in proportions of 0.5 to 5.0% of the weight of the rubber or polymer.  The substituted phenol may be mixed with rubber or rubber latex along with vulcanising and other ingredients such as anti-oxidants, pigments, fillers, plasticizers and blowing agents and the resulting mixes cured by heat treatment, or the mixture may be vulcanised by treatment with sulphur monochloride in the cold. Antiozonant effect is enhanced by the addition of paraffin or microcrystalline wax. When used for the preservation of polymers such as polyethylene or polypropylene, other antioxidants, e.g. an alkyl thiodipropionate may be added.ALSO:Antioxidant and antiozonant stabilizers for mineral oils, e.g lubricating oils and motor fuels, comprise phenols substituted in each of the 2, 4 and 6 positions by substituents one of which is a benzthiazylthioalkyl group of formula <FORM:0957842/C3/1> where R and R1 are hydrogen atoms or alkyl groups and the nucleus A may be substituted by a chlorine atom or an alkyl, alkoxy or alkylamino group, the second is another such benzthiazylthioalkyl group or a tertiary alkyl or alkylcycloalkyl group, and the third is an alkyl group having up to 9 carbon atoms, an alkylene group joined to another phenol nucleus having a benzthiazylthioalkyl substituent (said phenol being optionally substituted by a chlorine atom), or a cycloalkyl, alkylcycloalkyl or aralkyl group (see Division C2).